ChemicalBook CAS DataBase List 4-(3-NITRO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER

4-(3-NITRO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER synthesis

4synthesis methods

Product Name:4-(3-NITRO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER
CAS Number:116904-71-3
Molecular formula:C12H13NO5
Molecular Weight:251.24

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37517-78-5 Synthesis

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4-(3-NITRO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER

116904-71-3
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Yield:-

Reaction Conditions:

with 1,1'-carbonyldiimidazole in tetrahydrofuran

Steps:

111.1 4-[3-[[[(3R,5S)-7-Chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]amino]phenyl]butanoic acid
(1) To a solution of 3-nitrophenylacetic acid (10 g, 55.2 mmol) in tetrahydrofuran (100 ml) was added carbonyldiimidazole (10.5 g, 65.0 mmol). After stirring at room temperature for 6 hours, magnesium salt of monoethyl malonate (9.3 g, 32.5 mmol) were added thereto. The mixture was stirred at 60° C. for 3 hour. Then, the reaction mixture was diluted with ethyl acetate (100 ml) and washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline. After drying with sodium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography [eluent:hexane-ethyl acetate (1:1)] to obtain ethyl 4-(3-nitrophenyl)-3-oxobutanoate (10.0 g, 39.8 mmol, 72%) as a colorless amorphous powder. IR ν_max (KBr) cm^-1: 1745, 1722 (C=O). ¹H-NMR (CDCl₃) δ: 1.297 (3H, t, J=7.4 Hz), 3.544 ({fraction (9/10)}*2H, s), 3.606 ({fraction (1/10)}*2H, s), 4.005 ({fraction (9/10)}*2H, s), 4.195 ({fraction (1/10)}*2H, q, J=7.4 Hz), 4.223 ({fraction (9/10)}*2H, q, J=7.4 Hz), 4.982 ({fraction (1/10)}*1H, s), 7.52-7.55 (2H, m), 8.08-8.19 (2H, m).

References:

Kori, Masakuni;Miki, Takashi;Nishimoto, Tomoyuki;Tozawa, Ryuichi US2003/78251, 2003, A1